CH535263A - Verfahren zur Herstellung von Pyrazolo-(thiono)-phosphor (phosphon)-säureestern - Google Patents
Verfahren zur Herstellung von Pyrazolo-(thiono)-phosphor (phosphon)-säureesternInfo
- Publication number
- CH535263A CH535263A CH1779371A CH1779371A CH535263A CH 535263 A CH535263 A CH 535263A CH 1779371 A CH1779371 A CH 1779371A CH 1779371 A CH1779371 A CH 1779371A CH 535263 A CH535263 A CH 535263A
- Authority
- CH
- Switzerland
- Prior art keywords
- active ingredient
- formula
- sep
- compound
- solvent
- Prior art date
Links
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- 150000002148 esters Chemical class 0.000 title description 6
- 230000000895 acaricidal effect Effects 0.000 title description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 230000001419 dependent effect Effects 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 56
- 238000012360 testing method Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 239000003995 emulsifying agent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
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- 238000006243 chemical reaction Methods 0.000 description 7
- -1 heterocyclic amines Chemical class 0.000 description 7
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
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- 235000014066 European mistletoe Nutrition 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
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- 229930186364 cyclamen Natural products 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000001119 rodenticidal effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702060198 DE2060198A1 (de) | 1970-12-08 | 1970-12-08 | Pyrazolo-(thiono)-phosphor(phosphon)-saeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH535263A true CH535263A (de) | 1973-03-31 |
Family
ID=5790250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1779371A CH535263A (de) | 1970-12-08 | 1971-12-06 | Verfahren zur Herstellung von Pyrazolo-(thiono)-phosphor (phosphon)-säureestern |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3808227A (cs) |
| AT (1) | AT304578B (cs) |
| AU (1) | AU3532371A (cs) |
| BE (1) | BE776409A (cs) |
| BR (1) | BR7108129D0 (cs) |
| CA (1) | CA935435A (cs) |
| CH (1) | CH535263A (cs) |
| DE (1) | DE2060198A1 (cs) |
| DK (1) | DK130304B (cs) |
| FR (1) | FR2117533A5 (cs) |
| GB (1) | GB1315888A (cs) |
| HU (1) | HU163828B (cs) |
| IL (1) | IL38299A (cs) |
| IT (1) | IT946127B (cs) |
| NL (1) | NL7116739A (cs) |
| TR (1) | TR16799A (cs) |
| ZA (1) | ZA718185B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2235947B1 (cs) * | 1973-07-05 | 1978-09-29 | Roussel Uclaf | |
| NL7812293A (nl) * | 1977-12-23 | 1979-06-26 | Montedison Spa | Fosforzuur en thiofosforzuuresters van 5(3)-hydroxypyrazolen met insecticide werking. |
| JPS5547695A (en) * | 1978-09-19 | 1980-04-04 | Takeda Chem Ind Ltd | Pyrazole phosphate, its preparation, and insecticide and miticide |
-
1970
- 1970-12-08 DE DE19702060198 patent/DE2060198A1/de active Pending
-
1971
- 1971-11-04 AU AU35323/71A patent/AU3532371A/en not_active Expired
- 1971-12-02 US US00204312A patent/US3808227A/en not_active Expired - Lifetime
- 1971-12-06 CH CH1779371A patent/CH535263A/de not_active IP Right Cessation
- 1971-12-06 IL IL7138299A patent/IL38299A/xx unknown
- 1971-12-06 NL NL7116739A patent/NL7116739A/xx unknown
- 1971-12-06 IT IT32113/71A patent/IT946127B/it active
- 1971-12-07 TR TR16799A patent/TR16799A/xx unknown
- 1971-12-07 GB GB5680871A patent/GB1315888A/en not_active Expired
- 1971-12-07 AT AT1052071A patent/AT304578B/de not_active IP Right Cessation
- 1971-12-07 CA CA129507A patent/CA935435A/en not_active Expired
- 1971-12-07 ZA ZA718185A patent/ZA718185B/xx unknown
- 1971-12-07 DK DK599271AA patent/DK130304B/da unknown
- 1971-12-08 BE BE776409A patent/BE776409A/xx unknown
- 1971-12-08 BR BR8129/71A patent/BR7108129D0/pt unknown
- 1971-12-08 HU HUBA2676A patent/HU163828B/hu unknown
- 1971-12-08 FR FR7144051A patent/FR2117533A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL38299A (en) | 1974-05-16 |
| DE2060198A1 (de) | 1972-06-15 |
| NL7116739A (cs) | 1972-06-12 |
| CA935435A (en) | 1973-10-16 |
| IL38299A0 (en) | 1972-02-29 |
| FR2117533A5 (cs) | 1972-07-21 |
| BE776409A (cs) | 1972-06-08 |
| IT946127B (it) | 1973-05-21 |
| DK130304C (cs) | 1975-06-30 |
| HU163828B (cs) | 1973-11-28 |
| DK130304B (da) | 1975-02-03 |
| TR16799A (tr) | 1973-05-01 |
| AT304578B (de) | 1973-01-10 |
| ZA718185B (en) | 1972-08-30 |
| BR7108129D0 (pt) | 1973-05-17 |
| US3808227A (en) | 1974-04-30 |
| GB1315888A (en) | 1973-05-02 |
| AU3532371A (en) | 1973-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |